Potassium Carbonate → 4-Methoxy-2-(3',4',5'-tris(octadecyloxy)cyclohexylmethyloxy)benzaldehyde

HRID 1502543Notes

Reaction equation

HRID 1502543 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH:6]1[CH2:11][CH:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:9]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH:8]([O:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68])[CH2:7]1)(=O)=O.[OH:76][C:77]1[CH:84]=[C:83]([O:85][CH3:86])[CH:82]=[CH:81][C:78]=1[CH:79]=[O:80].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(Cl)(Cl)Cl>[CH3:86][O:85][C:83]1[CH:82]=[CH:81][C:78]([CH:79]=[O:80])=[C:77]([O:76][CH2:5][CH:6]2[CH2:11][CH:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:9]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH:8]([O:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68])[CH2:7]2)[CH:84]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 594992363,4,5-Tris(octadecyloxy)cyclohexylmethyl tosylate

Product 1

HCID 866548934-Methoxy-2-(3',4',5'-tris(octadecyloxy)cyclohexylmethyloxy)benzaldehydeYield 97.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3,4,5-Tris(octadecyloxy)cyclohexylmethyl tosylate (76.9 g, 71.6 mmol), 2-hydroxy-4-methoxybenzaldehyde (16.9 g, 0.11 mol) and potassium carbonate (25.6 g, 0.18 mol) were suspended in DMF (700 ml), and the mixture was stirred at 80° C. overnight. The reaction mixture was dissolved in chloroform (700 ml), washed twice with 0.5N hydrochloric acid (300 ml), once with 5% aqueous sodium hydrogen carbonate solution (300 ml), and once with pure water (300 ml). The solvent was evaporated, and the residue was precipitated with methanol (700 ml) to give 4-methoxy-2-[3′,4′,5′-tris(octadecyloxy)cyclohexylmethyloxy]benzaldehyde (73.56 g, 69.8 mmol, 97%).

Workup

  1. washwashed twice with 0.5N hydrochloric acid (300 ml), once with 5% aqueous sodium hydrogen carbonate solution (300 ml)
  2. customThe solvent was evaporated
  3. customthe residue was precipitated with methanol (700 ml)

Sources & evidence

ORD record
ord-6c362588b05241af8abb8d6c697925f6
Source dataset
uspto-grants-2015_12
Patent number
US09206230B2

Reaction notes

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